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Volume 66 
Part 10 
Page o2637  
October 2010  

Received 16 September 2010
Accepted 20 September 2010
Online 25 September 2010

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.001 Å
R = 0.039
wR = 0.122
Data-to-parameter ratio = 18.5
Details
Open access

1,3,5-Triazaadamantan-7-amine

aDepartment of Chemistry, University of Victoria, PO Box 3065, Victoria, BC V8W 3V6, Canada, and bUniversity of Notre Dame, Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA
Correspondence e-mail: aoliver2@nd.edu, mcindoe@uvic.ca

The title compound, C7H14N4, represents the first structurally characterized, isolated triazaadamantane. In the crystal structure, weak intermolecular N-H...N hydrogen bonds link the molecules into columns about the crystallographic fourfold axis.

Related literature

For general background to applications of the title compound and its preparation, see: Hodge (1972[Hodge, E. B. (1972). J. Org. Chem., 37, 320-321.]); Karelina et al. (1987[Karelina, V. N., Goncharov, V. M., Mirontseva, T. V., Delektorskii, A. A. & Orekhov, S. V. (1987). USSR Patent SU1359277, December 12, 1987.]); Kuznetsov et al. (2001[Kuznetsov, R. M., Balueva, A. S., Serova, T. M. & Nikonov, G. N. (2001). Russ. J. Gen. Chem. 71, 899-902.]); Nielsen (1975[Nielsen, A. T. (1975). J. Heterocycl. Chem. 12, 161-164.], 1977[Nielsen, A. T. (1977). 7-(N-Methyl-N-Alkylamino)-1,3,5-Triazaadamantanes. US Patent 4012384, March 15, 1977.]); Safar et al. (1975[Safar, M., Galik, V., Kafka, Z. & Landa, S. (1975). Collect. Czech. Chem. Commun. 40, 2179-2182.]). For related structures, see: de Namor et al. (2008[Namor, A. F. D. de, Nwogu, N. A., Zveitcovich-Guerra, J. A., Piro, O. E. & Castellano, E. E. (2008). J. Phys. Chem. B., 113, 4775-4780.]).

[Scheme 1]

Experimental

Crystal data
  • C7H14N4

  • Mr = 154.22

  • Tetragonal, P 42 /n

  • a = 15.5402 (8) Å

  • c = 6.5074 (7) Å

  • V = 1571.5 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.32 × 0.24 × 0.15 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: numerical (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS University of Göttingen, Germany.]) Tmin = 0.973, Tmax = 0.987

  • 15555 measured reflections

  • 1960 independent reflections

  • 1662 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.122

  • S = 1.52

  • 1960 reflections

  • 106 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N11-H11A...N3i 0.898 (12) 2.335 (13) 3.2316 (13) 176.0 (12)
N11-H11B...N11ii 0.895 (14) 2.253 (14) 3.1465 (14) 175.2 (11)
Symmetry codes: (i) x, y, z-1; (ii) [-y+{\script{3\over 2}}, x, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: XP (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]) and POV-RAY (Cason, 2003[Cason, C. J. (2003). POV-RAY. Persistence of Vision Raytracer Pty Ltd, Victoria, Australia.]); software used to prepare material for publication: XCIF (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2767 ).


Acknowledgements

Data were recorded on an instrument supported by the National Science Foundation, Major Research Instrumentation (MRI) Program under grant No. CHE-0521569.

References

Bruker (2005). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA.
Cason, C. J. (2003). POV-RAY. Persistence of Vision Raytracer Pty Ltd, Victoria, Australia.
Hodge, E. B. (1972). J. Org. Chem., 37, 320-321.  [CrossRef] [ChemPort]
Karelina, V. N., Goncharov, V. M., Mirontseva, T. V., Delektorskii, A. A. & Orekhov, S. V. (1987). USSR Patent SU1359277, December 12, 1987.
Kuznetsov, R. M., Balueva, A. S., Serova, T. M. & Nikonov, G. N. (2001). Russ. J. Gen. Chem. 71, 899-902.  [CrossRef] [ChemPort]
Namor, A. F. D. de, Nwogu, N. A., Zveitcovich-Guerra, J. A., Piro, O. E. & Castellano, E. E. (2008). J. Phys. Chem. B., 113, 4775-4780.
Nielsen, A. T. (1975). J. Heterocycl. Chem. 12, 161-164.  [CrossRef]
Nielsen, A. T. (1977). 7-(N-Methyl-N-Alkylamino)-1,3,5-Triazaadamantanes. US Patent 4012384, March 15, 1977.
Safar, M., Galik, V., Kafka, Z. & Landa, S. (1975). Collect. Czech. Chem. Commun. 40, 2179-2182.  [ChemPort]
Sheldrick, G. M. (2008a). SADABS University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2010). E66, o2637  [ doi:10.1107/S1600536810037657 ]

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